Saylor's stance is rooted in his belief that Bitcoin is a superior form of money and a long-term store of value, destined for continued appreciation. He argues that waiting for pullbacks or corrections means missing out on the compounding gains that accrue over time, even from purchases made at what appear to be peak prices. For him, every new ATH is simply a step on a much longer upward journey.
The "leaving money" argument posits that given Bitcoin's historical performance and its fundamental characteristics, any price point, even an all-time high, is a relatively low entry point in the grand scheme of its future potential. Saylor implies that hesitation leads to opportunity cost, as Bitcoin tends to establish new floors after reaching new highs.
This perspective challenges conventional investment wisdom that often advises caution at market peaks. For investors, Saylor's view encourages a long-term, conviction-based approach to Bitcoin acquisition, prioritizing consistent accumulation over attempts to time the market. His comments reinforce the idea that in a truly scarce and appreciating asset, today's high could be tomorrow's low.